


Dean Winchester's Christmas Carol

by casstayinmyass



Category: Supernatural
Genre: 18th Century, Alternate Universe - A Christmas Carol Fusion, Canon Lesbian Character, Castiel Has a Crush on Dean Winchester, Christmas, Clerk Castiel, Closeted Dean, Dean Being an Asshole, Dean-Centric, Emotionally Repressed, F/F, F/M, Gay Dean, Implied Bottom Dean, Inspired by A Christmas Carol, Internalized Homophobia, John Sent Dean To Boarding School Because He Was Gay, John Winchester's A+ Parenting, John is a dick, M/M, Minor Character Death, Money, Period-Typical Homophobia, Sam Being an Asshole, Sexual Repression, Three Spirits, based on Charles Dickens, cas being adorable, destiel christmas, no surprise there
Language: English
Status: Completed
Published: 2015-12-26
Updated: 2015-12-26
Packaged: 2018-05-09 10:59:39
Rating: Teen And Up Audiences
Warnings: Creator Chose Not To Use Archive Warnings, No Archive Warnings Apply
Chapters: 5
Words: 12,721
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/5537396
Author URL: https://archiveofourown.org/users/casstayinmyass/pseuds/casstayinmyass
Summary: <blockquote class="userstuff">
              <p>Dean Winchester has become a miserable money-lender, unhappily rich owner of the family business, Winchester & Sons. On top of hating people, Dean also hates Christmas, because of all the misfortune it's brought his family. Castiel Novak is his penniless clerk, who is, for some strange reason, hopelessly in love with the man. On Christmas Eve, Dean gets a visit from his dead brother, warning him to change or face an eternity of loneliness and hardship. Dean hardly believes him, but three spirits are about to change his mind when it comes to spending his life with someone, and what's been sitting in front of his nose for years...</p>
            </blockquote>





	1. Christmas Eve

**Author's Note:**

> Merry Christmas, #SPNFamily!!! <3

 

Chuck Dickens opened a big, hardcover book after pulling it from the shelf. He blew the dust off, and opened it, smiling as he began to read the story he had written.

**_Sammy was dead, to begin with. As dead as a doornail, though I don't really claim to know how dead a doornail can particularly be..._ **

**_Regardless, Dean Winchester had watched his brother and business partner get sick. He had watched him die, and it had been the hardest moments of his life, especially when he had lost his sister at such a young age as well._ **

**_Now, the eldest Winchester was the only surviving sibling, the only one to carry on the family business. He was a money lender at Winchester and Sons, the business his father had started years ago. In this day and age, business was booming; and Dean was rich as rich could be._ **

**_Rich didn't exactly mean content, mind. Yes, he lived in a large house with expensive suits and bags of money in his safe, but he spent every night alone, in his dark, cold house. He never used to be a pleasant man when he first took over the business with Sam, but now, he was ten times worse; at only 34 years of age, he had since given up the chance to spend his life with someone._ **

**_For who could love a squeezing, wrenching, grasping, scraping, clutching, covetous, sinner such as Dean?_ **

-0-0-0-

The icicles on the door shook as wind blew by the sign that read "Winchester and Sons". Inside, it wasn't much warmer; Dean wouldn't spare a piece more of coal for the fire. Too expensive.

Dean sighed, putting his pen down on his book.

"Would you stop shivering?" he snapped at his clerk, who was sitting in front of him and chattering his teeth.

Castiel looked up, and blinked a few times. "S-sorry, sir. It's j-just that... the temperature... is a little low."

Dean rolled his eyes. "You know how expensive coal is these days? Ridiculous. It's comin' out of my money, not yours, so clam up and get back to work."

Cas nodded reluctantly, and blew on his hands to warm them up a little as he went back to work. When Dean looked back to his own book and picked up his pen again, he didn't notice Castiel sneak a second glance at him, this one longer.

"Did I stutter when I said WORK?!" Dean barked, and Cas jumped in his seat, shaking his head and starting to write.

Dean sighed, and muttered to himself, "God, if I could pay you any less..."

Cas looked up, sadness in his eyes, but since he did not wish to risk getting yelled at again by his employer, turned back to his bookkeeping.

Dean frowned. The man was always staring at him... Dean couldn't, for the life of him, figure out why. Of course, he didn't exactly mind someone as handsome as Cas staring at him, but that was a fact nobody ever needed to find out. He was strange, anyway... and got on Dean's nerves a lot.

Just as he was getting back into the thoughts of his business, the door clanged open, leaving Dean to groan.

"What now?!"

"Dean!" a female voice called, and he looked up to see his cousin, Charlie walking in.

"Charlie... now's not a really good time, I'm very bus-"

"Save it. I come bearing gifts!" the redhead smiled, and plopped a present down on Dean's desk. Dean looked at it sourly, and Charlie raised an eyebrow.

"So... Merry Christmas!"

Dean scowled. "You know I hate Christmas. Sam died on Christmas. Come to think of it, so did Jo. It marks nothing but bad luck."

"Oh come on, don't be so superstitious! Christmas is a time for giving, family!"

"Yeah?" Dean grumbled, "Where's our family? Oh yeah- rotting away in their coffins."

Charlie frowned at him. "Why don't you turn that frown upside down, and come for Christmas dinner with Gilda and me tomorrow night."

Dean scoffed. "God, why'd you get married, huh? To a penniless girl, no less?"

Charlie narrowed her eyes. "Because I fell in love... duh! Money isn’t everything."

Dean rolled his eyes. "That's even more ridiculous than a merry Christmas."

Charlie sighed. "Look, I know you hate this holiday... so, I'll just leave you with your gift, and... hopefully we'll see you tomorrow night."

She turned heel, and patted Cas' desk as she went by. "Merry Christmas, Cas," she smiled, and Cas smiled back.

"Merry Christmas, Charlie!" he called back, his face breaking into an endearing grin.

Dean just scowled again at them both, and went back to work when his cousin had officially left, not before dropping the gift that she had brought him in the waste bin underneath his big wooden desk.

Then, he returned to his work, getting as much as five whole minutes in before the door opened again. He growled low in his throat, and looked up to see two more people at his door. One was tall with kind brown eyes and a beard, holding a pipe in one hand, and the other was short, with black hair swept to the side holding a tin for coins.

“What is it?” Dean asked, “Can’t a man get any work done around here?”

“Afternoon, sir,” the first one said, tipping his hat, “I’m Benny, this is my partner, Kev. We’re tryin’ to raise a fund for the poor and destitute this cold winter season.”

Dean stared at them blankly as they went on.

“Have we the pleasure of addressing Dean or Samuel Winchester?”

Dean grunted. “Sam’s been dead for seven years. Seven years this very night, actually.”

Benny’s mentioned partner, Kevin, looked down. “W-were sorry to hear that, sir. I’m sure his Christmas spirit is well represented in his, um, brother.”

Dean scoffed at this, and Cas even looked up.

“So… at this festive time of the year, Mr. Winchester, we’d like to do as much as we can,” Benny explained, and smiled warmly. “What can I put you down for, now?”

Dean glared at the cheery pair. “Nothing.”

“Oh. Well now, that’s alright if you’d like to remain anonymous-“

“I want to be left alone,” Dean grumbled, tightening his fist on the desk, “I don’t celebrate Christmas myself, gentlemen, so I’d be very happy and very merry if you’d kindly use the door.”

Benny looked taken aback, and Kevin stuttered.

"What about the h-homeless?!"

"Put 'em in prison, I don't know."

Kevin gulped. "Many would rather die than go there!"

"Fine, then! If they'd rather die, why don't they just do it, and decrease the surplus population! For Christ's sake..."

Kevin and Benny looked at each other, and Benny spoke up again softly.

"I see we've taken enough of your time. Let's go."

“Uh… Merry Christmas to you anyway, sir?” Kevin tried.

Dean clenched his jaw. “Every idjit who goes around with ‘ _Merry Christmas’_ on his lips should be baked with his own pie and buried with a stake of holly through his balls.”

Kevin whimpered, and Benny frowned, putting his hat back on. “Good afternoon to ya.”

Dean just watched them leave, but as they were walking away, Cas suddenly called them back.

“Wait! Pardon me gentlemen, but… I believe I have something to give,” he mumbled, digging around in his pockets, and finally came out with a coin. “I’m sorry it isn’t more,” he said softly, and Kevin smiled.

“Thank you! You’re a real gent.”

Cas smiled, and sat back down. Dean looked up at him, and laughed coldly.

“What was that, half of your pay for this week?”

Cas swallowed. “There are others who need it more than I do, sir.”

Dean frowned, and shook his head at his clerk’s idiotic logic.

-0-0-0-

Sooner than expected, it was the end of the day, the clock striking seven. Dean laid down his pen, and checked to make sure the clock was working properly.

“Well… I guess that’s a day,” he muttered, and turned around. “I’ll see you bright and early tomorrow morning, Novak.”

Cas looked up nervously, and bit his chapped bottom lip.

“Mr. Winchester, sir… it’s Christmas tomorrow.”

Dean looked unphased. “…And?”

Cas looked down, fiddling with the hole in his worn suit.

“Um… is it not customary to give workers the day off? Sir?”

Dean scowled, as he had been in the habit of doing that day. “It’s a piss-poor excuse for picking a man’s pocket every December the 25th.”

Cas sighed, nodding in defeat, and got up slowly, wondering what he would tell his brother and sister-in-law, Jimmy and Amelia Novak, who were visiting with his little niece Claire tomorrow for the holiday. Poor little Claire would be so disappointed…

“-But it seems that I’m the only one who knows it’s robbery,” Dean continued, shaking his head. “Take the day off, dammit.”

Cas looked up again with a surge of joy, a smile overtaking his face. Dean knew it was more than kind to give his clerk the day off, but he didn’t do it just because it was bad for business; there was some sort of warmth pitted in his stomach when he saw Castiel smile like that. It didn’t last for long, though.

“Oh, thank you so much, sir!” Cas said, grinning, “Thank you a hundred times over! Is there anything I can do for you?”

Dean snapped his head up at this, and frowned, re-adjusting his tie. “Yeah- you can shut up and get out.”

Cas closed his mouth, and nodded quickly, a little hop in his step this time as he got his scarf and hat on.

“Merry Christmas, Mr. Winchester!” Cas said with a blush as he held the door open for his employer. The clerk looked like he was about to say something else, but bit his lip. Dean eyed him curiously.

“Right…” he finally said, and left, the hard soles of his expensive shoes clicking against the icy cobble street as he made his way home. Cas went the opposite way, still smiling as he hummed to himself.

That man has no right to be so happy, Dean thought to himself bitterly with yet another scowl, He’s so goddamn poor, he doesn’t have any reason to be. Sometimes, people just mystified Dean. But then again, a point that he was overlooking was the fact that he was miserable while having too much money to count.

Over in the other end of the city, the poorer end, little Claire looked into the window of a toy shop. She gazed around in awe of the toys, toys she would never get as a present.

"Sweetheart, come along," Amelia smiled, who was walking with her husband Jimmy, "We don't want to be late to Uncle Cas', do we?"

Claire gasped, and hurried her walking, latching onto Jimmy's arm for support.

"Not at all! I can't wait to see Uncle Cas!"

Her parents smiled at her.

-0-0-0-

Dean sighed out a breath of frigid winter air, and came up to his place, walking up the stairs carefully in the dark. He found it funny to imagine he might slip, thereby joining his two siblings in their unfortunate Christmas downfalls. Wouldn’t that be a laugh…

He took out his ring of keys, and unlocked the door, finding the right one. Just as he was unlocking it and preparing to enter his den of solitude for the night, he caught movement inside the house from the peephole. He frowned, and looked in. There, standing and looking right back at him, he saw-

“Sam?!” he cried, stumbling back. No… no, this couldn’t be right… Sam was… Sam was dead, but it couldn't have been anyone else, Miss Masters, his maid, had gone home…

He held onto the stairway railing, and caught his breath. He looked back, and saw nothing in his foyer through the glass.

“You stupid son of a bitch,” he told himself with a throaty chuckle, “Your brother’s dead and buried.”

He felt a stab of something like disappointment, but how could he be disappointed about something that had happened seven years ago? Yes, he loved Sam more than the world… but that’s why he hated Christmas. It was just a reminder of everyone’s happiness in contrast with his own gloomy life. He could barely even remember what love felt like anymore.

He unlocked the door fully, and hung up his hat and coat, starting up the stairs. His home was just as dark, foreboding, and cold as his place of business, even more so at night; but it affected him not. He was used to it, and darkness was cheap, which he also liked.

He went into his bedroom, and sat down with some bread and leftover pie he had. He poured himself some fine whiskey, and got down to drinking, hoping he could just drink himself into a lull and miss Christmas altogether.

Just as he was raising the last piece of rather stale apple pie up to his mouth, he heard a noise.

It was the typewriter.

He turned fearfully, and watched the mechanism. That was Sam’s favorite thing to do in his life; type away at that thing. He used it all the time… Dean had almost forgotten what it sounded like since.

 _All of this is foolish,_ he thought to himself, _all of it! I’m hearing things. It’s just the grief, nothing more._

He attempted to get back to eating his pie, but was once again disturbed by the sound of the typewriter going. This time, Dean was sure he was not hearing things, and his heart started to pound in time with the keys smacking on invisible paper.

Suddenly, he heard what sounded like chains on the stairs just outside his door, and his hand flew to grip the armchair he was sitting in. The awful sound of the chains grew closer and closer, until finally, they stopped at the door. Dean contemplated hiding, but that would mean he believed what he heard, which he most certainly didn’t.

There was more silence, but Dean could hear the faint clanking of something behind the wood.

“Show yourself!” Dean shouted, wondering if he had gone mad and was shouting at nothing. He was prepared to assume the latter after more silence that followed, until a young man appeared on his side of the door, clear as day.

“Sammy,” Dean breathed, eyes widening. Now, he was sure of it. He had gone mad.

“Dean,” Sam said, though he sounded distant, almost unreal. The elder, more alive brother felt tears welling up in his dull green eyes. He hadn’t heard that voice in years…

“My god, this stuff must be strong,” Dean huffed, sniffing away the tears, and picked up the bottle of whiskey to stare at it long and hard.

The apparition of Sam walked forward a few steps closer, and frowned. “You don’t think it’s really me?”

Dean laughed, and shook his head. “You’re dead.”

“But you see me, right? I’m right here, talking to you.”

“Yeah, but you’re not…” Dean tried, searching for words as he gazed almost right through the translucent form, “You’re different.”

“Am I?” Sam asked, walking closer. Dean drew back uncomfortably, and Sam sat down in the chair across from him, dragging the chains he pulled with him.

He laughed, though it sounded croaky and like a knife dragging on stone. At least he didn't have that horrible cough anymore.

“I’m your brother, Dean. You really scared of your own brother?”

“When my brother’s supposed to be six feet under? Yeah, kinda.”

“Yeah, well,” Sam sighed, looking into the ashy fireplace, “I need to talk to you.”

“Good mercy, I must be sauced,” Dean muttered, and with a shrug, he refilled his glass. "You could just be a bit of stale pie... a blob of underdone cream, makin' me imagine this!"

“Dean,” Sam said, a little more forcefully, “Listen to me.”

“Why should I?” Dean snapped, looking up at the vision of his little brother. He looked sickly, pale, and Dean hated seeing him how he was the day he died. “I’d only be talking to myself, ‘cause I’m making this up!”

“You’re not,” Sam said simply, and Dean ran a hand through his hair.

“You can’t be Sam,” he hissed, “Sam is DEAD! GONE! BURIED, DAMMIT!” he shouted, downing the glass of whiskey and going to pour another. Sam got up from his seat, and grabbed the bottle out of his brother’s hand with icy, transparent fingers, and sent it smashing into the wall.

“LISTEN TO ME!” Sam shouted, and Dean froze, seemingly irritated.

“That was an expensive bottle…”

“You see, Dean?!” Sam huffed, shaking his head, “This is what I’m here to talk to you about. Everything with you is money! It’s all about wealth, gain, being rich!”

Dean shifted. “Nothing wrong with making a few more than the next man.”

“Well, it’s wrong when you evict the next man for paying a day late!”

This shut Dean up, and his brother sighed. “Look… you’ve only got once chance, Dean. I’m trying to save you, here.”

“Save me?” Dean frowned, “How can a hallucination save me?”

“For the last time, I’m not a hallucination!” Sam groaned, and looked down at his chains. “Here, feel these- do they feel fake to you?”

Dean reached out cautiously, and felt how awfully heavy the metal chains were.

“Why do you carry them around, huh?”

“I made them while I was alive,” Sam sighed, sitting down again, “I created them, a link for every selfish deed I did, and I did a lot. I took people's money, and I hurt the most beautiful creature alive, who loved _me_ of all people. But see, I died before I could make the chain longer- you’ve got no idea how long yours is!”

This frightened Dean, and he gulped. “Well… you were just doing your job. I’m just doing mine.”

Sam shook his head. “No, no, Dean, it’s not your job to be cruel. Dad taught us to be ruthless with people, right? He taught us that gain is everything, that nobody deserves a second chance.”

“Yeah,” Dean nodded, “Smart businessman, dad was.”

“Well he was a miser, Dean! Like you and I became. I know you deserve a second chance! I know you, Dean. You can change!”

“Change?” Dean asked, “What are you talking about?!”

“You knew mom,” Sam said softly, tears forming in his eyes, if that was even possible for a spirit, “You knew her before I was born, before she died giving birth to me. She was good! From what I hear, that woman was so lovely... Remember her- and maybe that can remind you what it is to be good again. What it is to love.”

Dean averted his eyes, and looked over to the broken bottle of alcohol. "What turned you into Mr. Nice Guy?" Dean asked, and Sam raised an eyebrow.

"Dragging chains around sure helps!"

Dean smirked. "Well, you always were the buffer one- I'm sure you can handle it." Sam glared.

"This is NOT the time to be funny, Dean. It's long past that. Take it seriously, because you sure will when you end up like me." Sam took Dean's silence as an invitation to continue. “You’ll be visited by three spirits tonight,” Sam told him, leaning back.

“Three?” Dean squeaked, still not used to the fact that he was actually conversing with his deceased brother, “Three more? Why?!”

“You need them,” Sam replied with an eye roll, and Dean swallowed nervously.

“Can’t they just… I don’t know… all come at once?”

“No, that’s not how it works, Dean,” Sam shot back, and Dean raised his eyebrows; even in death, his brother could pull a withering bitchface. “I have to go,” Sam muttered, “I carry these chains around for eternity. I can’t stay in one place for too long, but please, I’m begging you- change, Dean.”

Dean watched Sam as he gave a small, sad smile, and disappeared just as abruptly as he had appeared in the first place. He sat in returned silence for five minutes before he could get the courage to stand and actually trust his legs to work, and walked over to the liquor cabinet in his room for more.

It would be a long night.

 


	2. Past

-0-0-0-

One O' Clock. Dean couldn't sleep, so he recognized the chiming of the time. He laughed to himself as he heard no chains, no moaning or wailing, no bumps or typewriters typing. Nothing strange or out of the ordinary; guess he had just been drunk out of his mind. He still was, honestly- so he closed his eyes again, hardly fretting over what sort of hangover he would have the next day.

Suddenly, as he was about to roll over and toddle to sleep finally with calmed nerves, a blinding light shone through his bed curtains.

"What the-?" He muttered, and huddled into his covers, scared to draw back his curtains. No matter- that was evidently done for him. As the brilliant light faded, a face appeared, and then a (nice-looking) body to accompany it. It was a young, beautiful woman, with hair as black as night down to her shoulders, and skin as pale as the moon. She was clothed in a long white dress.

"Are... are you the ghost whose coming was foretold?" Dean slurred, and the woman smiled.

"I am."

"What's... what's your name?"

She chuckled. "I'm the ghost of Christmas past, but you can call me Tessa." Dean nodded slowly.

"Well, sorry honey, but I'm pretty drunk... I'd better go back to sleep." She raised an eyebrow.

"I have appointments to keep, Dean. Get up, or I'll get you up." Dean coughed a little, and she held out her hand.

"Here... touch my hand, and you'll be able to think clearly."

Dean hesitated, wondering if he was dreaming and should just get back into bed, but he had since come to terms with the fact that this might very well be real.

"What the hell," Dean shrugged, and, pulling his nightgown closer to him, got up, reaching out to touch Tessa's arm. In a second, his mind was clear, and he did not feel intoxicated anymore, for better or for worse.

"Come," Tessa said, and Dean gulped as she opened the window.

"Uh... sorry, but... I'm mortal, y'know? And, uh... I can't really fly?"

Tessa grinned. "C'mon, Dean. Where's your sense of adventure?" With that, the spirit took his arm, and they were transported through another white light to wherever they were going... which, as it turns out, was the past. Dean's, to be exact.

They finally stopped, and a world materialized around them. It was the scene of a snowy day, and an old schoolhouse standing proud and tall beyond the trees.

"So... you recognize it?" Tessa asked, crossing her arms and leaning against a trunk.

"R-recognize it?" Dean asked, swallowing shakily, "God, yeah! I grew up here! I trained here! I-" he coughed, rubbing the back of his neck, "Became a man here, in more ways than one..."

Tessa smirked, and she waved her hand, bringing the two of them into the schoolhouse, and Dean bit his lip when he saw a boy sitting there.

"You can't be more than... mmm... 16, here?" Tessa said, smiling fondly, "Back then, you didn't have any family that wanted you home for Christmas. That is, of course, until this one."

Dean watched as the doors burst open, and in ran a young blonde girl in a black dress and bonnet.

"Jesus," Present-Dean breathed to himself, fighting back tears, "It's..."

"Joanna Beth Winchester," Tessa nodded, regarding the little girl, "Your only sister. Died when she herself was 16, of cholera. She had a kind heart- unlike you and your brother."

"That's only because she was too young for Dad to teach her the proper ways of the world," Dean snapped, "She was too open-hearted and trusting... always took people for their word."

"She was a good person, who _believed_ in good. Remind you of anyone?"

Dean frowned for a second, then paled a little. "Charlie..."

"Yep. You treat Charlie horribly; she's just like Jo. Perhaps you would treat your own sister that way if she were still alive?"

Dean winced, and Tessa shrugged. "Anyway- watch."

Dean turned back, and saw Jo run over and wrap his younger self in a big hug.

"Woah there!" Dean grinned, picking her up, "Jo, what're you doin' here?!"

"Coming to get you for Christmas!"

"Jo... you know I can't do that. I can't go home to Dad, not after everything."

"He wants you home more than anything, trust me!" Jo explained. "Things have been bad. Real bad. Dad yells at Sam all the time, and Sam yells back. One night, I started crying, and asked if you could come home from school and father said yes! He said yes, Dean!"

Dean hesitated.

"Do you know why Dad sent me here?"

She shook her head, blinking.

Dean nodded slowly. "Good... but I don't know about going home..."

Jo tugged on his arm. "Please! Oh, please, Dean?!"

He grinned, the laugh lines around his bright green eyes crinkling, and nodded. "Alright. How can I say no to those puppy eyes, huh sweetheart?"

Jo laughed, and led him out to the coach waiting for him in the snow.

"So, have you found true love yet?" the girl giggled.

Dean blushed, and looked down at her. "Why're you always askin' me that?"

"Because maybe you'll be happier if you find some nice boy to love and kiss and get flowers for and stuff!"

Dean suddenly clenched his jaw, and frowned down at her. "Don't you ever say that out loud, do you hear me? Men don't like men. Not that way. I certainly don't, and I won't have my sister going around telling people I do."

"I'm sure you do... and why can't men like men?" Jo asked, eyes blinking up at him, and Dean sighed.

"Because if they do, their fathers will send them away," he muttered. 

Present-Dean sighed, looking away. Tessa put a hand on his back.

"That Christmas, your father had finally accepted you back into the household. When you expressed interest in other boys at age 7, he would have none of it, and sent you away to reformatory boarding school. You spent the years at the school going through hard times that nobody was there for you for... there were a couple of boys you spent the night with here and there, because it felt good to fall out of society's role and let someone else take care of you in a different way. Behind cosed doors, none were the wiser. You learned, you adapted, and you fought that feeling after a while, realizing that maybe John was right- there was something wrong with you. This year, you went back home, a changed man," Tessa said.

Dean nodded. "I had myself convinced I liked women after that. I didn't want a repeat of how lonely I felt here... I guess that just made me even more lonely."

Tessa continued. "Two years later, at 18 young years of age, you were offered your first job at the carriage maker's by Bobby Singer."

Dean's eyes widened, and he watched as the world in front of them dissolved into a place of business, a surly looking fellow with a beard rushing around.

"Bobby," Dean muttered, feeling a lump of regret form in his throat, "He was so nice to me." He looked down, suddenly thinking of something... of someone.

Tessa raised an eyebrow. "What?"

"Nah, nothing," Dean mumbled, then Tessa rolled her eyes.

"What?!"

"Okay, alright! My clerk... I'm just thinkin' about him... I don't pay him nearly enough, and he works for what he does get."

Tessa nodded a little. "Castiel is a good man. Not at all deserving of how you treat him."

Dean felt shame creep at him,  when suddenly, his almost-employer walked right through him.

The man who he'd known for years, Bobby Singer. When Dean had come back from boarding school as a young man, he had stopped one day to talk to a Bobby Singer about the carriage wheels on a coach, and like that, the two had instantly clicked. Bobby worked in that line of business, and Dean was fascinated with all of it. He wanted to know more, and Bobby would teach him how to build certain parts... he had become like a second dad.

One day, when he had turned eighteen, Bobby had offered to show Dean his workshop, which was the scene Tessa and the present-Dean were in.

Suddenly, they watched Dean, now a young man, walk in, astounded by everything.

"Wow!" Past-Dean exclaimed, "You make all of these?! Just like you showed me?"

"We do," Bobby grinned, "From scratch. Sound like something you're interested in doin'?" The owner may have seemed surly to the outsider's eye, but he had the warmest heart Dean had ever been lucky enough to get to know.

"Yeah!! I mean... yes, sir," Dean said, looking down. Bobby chuckled, and put a hand on his shoulder.

"Well, you sure are passionate about this stuff. I look forward to your contributions to the company, sir."

"Yeah... yeah, me too!" Dean grinned.

The scene suddenly dissolved into the place again, but this time, the mood felt dreary, disappointing.

"What happened here?" Dean asked nervously, and Tessa just raised an eyebrow at him.

"Don't you remember?"

Suddenly, that same younger version of Dean came walking right through them, and trudged up to Bobby, where he was working at a desk.

"Come to start work, m'boy?!" Bobby grinned, looking up, and in noticing Dean's downtrodden face, went to comfort him. "You okay, son?"

Dean blinked. "I... I can't work for you, Mr. Singer. My father won't allow it- he says," Dean sniffled, "He says I've got to carry on the family business of money lending. He said he didn't make the company just to sell it when he dies. He's making me and Sammy take over."

Bobby looked disappointed. He knew who Dean's father was; John Winchester, meanest man in town. Dean was nothing like him, and Bobby feared he would become more like his old man if he was apprenticed at this family business, but alas, it wasn't for him to dictate.

"I understand. Listen, son- if you ever need any work... come on out here. I'd be right proud to have an apprentice like you."

Dean smiled as best he could, and Bobby hugged him.

"That was my biggest regret," present-Dean said, wiping his eyes, "Turning down this job. I'd found my calling, then my dad had to go and force me into something I didn't want. Had to be the good son."

"You never forgave your father for that," Tessa said, "But you did learn the ways of the family business as he taught them. The next Christmas was even harder than this one on you, wasn't it?"

Dean frowned as he stopped to think, then paled. "Please... oh, please, spirit, if you have any heart at all, don't show me that one!"

Tessa smiled sadly. "It's because I do that I must."

Dean squeezed his eyes shut as Tessa waved her hand, and the scene dissolved into the sound of crying.

It was the scene of a bedroom, with a woman in the bed. Immediately, Dean's fears were confirmed as he saw the blonde hair sprawled out on the pillow. Then he heard his own voice.

"Jo... Jo, can you hear me?"

His sister roused a little, and the doctor put a hand on his shoulder. "Be gentle with her, sir."

"I am being gentle," 18-year-old Dean snapped at him, and looked back. "Jo, please... it's me, it's Dean..."

"Dean," she smiled, whispering his name out, " Sam came in not long ago... it was so good to see him... it's... so good to see you again... you came home to us... you came home to Sammy and me from school..."

Dean bit his lip, and wrapped his hand around her clammy one. "That... that happened four years ago, sweetheart."

Jo made an incoherent noise, and rolled her head around on the pillow. Present-Dean closed his eyes, but Tessa nudged him, making him watch.

"I can't... please don't make me watch her die, not again," Dean whimpered, but the scene played on. 

"Dean, promise me something..." Jo said, eyelids fluttering.

"Anything- anything Jo," Dean said, nodding, "Except... I won't need to, 'cause you're gonna get better!"

"No," Jo whispered, "I'm not."

"Yes, you are!" Dean sobbed, clutching her hand tightly, "I-If you're not around, who's gonna ask me if I've found true love yet, huh? Who's gonna ask me...?"

Jo didn't reply, only continued to breath harshly.

"Jo?" Dean asked, lip trembling, "Jo?!"

"Sir, I think you had better leave," the doctor said, but Dean just pushed him away.

"Jo, please! Please, answer me, you can't die!"

Tessa and Dean watched as the younger version of the man shook her, and the doctor escorted him out.

"When she died, the last of your humanity died with her," Tessa said quietly, "You truly became your father's son."

"Yeah," Dean croaked out, ducking his head so that the spirit wouldn't know he was crying. Then he turned to Tessa. "Why'd you show me that, huh? What was the point of showing me that all over again?"

Tessa just nodded to the bed, and Dean heard Jo continue, to his surprise.

"Dean... Dean, listen to me... take care of Sam... and be happy with someone, you hear me? Be... _happy_ with someone." A second later, her arm fell limp, and the doctor solemnly pulled the sheet over her head.

Dean gawked at the vision, and ran a hand through his hair.

"Oh god... oh god, Jo... I didn't hear... I..."

Tessa put a hand on his shoulder.

"Come. There is still much to see."

"I don't want to see anymore. No, take me home!" Dean said, rubbing at his eyes.

"Suck it up, it's your past," Tessa said, and waved her hand again. This time, Dean could see their dad talking to him and Sam, teaching them how to handle things in the business.

"My god," Present-Dean muttered, "Look at you, Sammy..." Sam was younger than when he had appeared to him earlier that night, with bangs and awkwardly strewn hair. It was kind of funny, if not gut wrenching, to see his brother like this again.

"Now, what did I say about being kind?" John asked, and as if drilled into their heads for the right answer, Dean replied, "Kindness has no place in business."

"That's right," John nodded sternly, "And what else?"

"Evict first, ask questions later," Sam said.

John nodded again. "I'm so proud of you boys- you've grown into dashing young men. You're gonna take over the company and run it well, I just know it."

Sam and Dean both thanked him, and John went over to the desk at the office, rooting through.

"Speaking of eviction, this'll be your first real call to action; we've got a business in town that hasn't paid off their borrowed expanse money."

Dean smirked. "This'll be fun- who?"

"Yeah, who?" Sam grinned.

John looked at the papers. "Singer's Carriages," he said, "Man borrowed a bunch of money for all the supplies he needed to develop, but can't pay it back just yet. Boo hoo, huh?"

Dean smiled weakly, feeling the blood drain from his face. "Y-yeah... who does he... who does he think he is?"

"You okay, Dean?" Sam asked, frowning, "You don't look so good."

"Fine," Dean mumbled, "L-let's do this."

They hopped into a coach, and made it over to the office that Dean spent so much time at in his youth. When they arrived, Bobby opened the door.

"Oh... hello," he said apprehensively, "Merry Christmas."

"Not for you," John replied, taking off his hat and gloves, and Dean winced. "You're being closed down because you haven't paid us back on time," his father continued, and Bobby opened his mouth.

"Now, wait a minute, please-"

"We have waited," John said sharply, "A lot of minutes. Sam, take the sign down. Dean, grab his assets."

Sam immediately dashed off to take down the sign above the door, but Dean froze on the spot. Bobby and John both looked over at him, and John frowned.

"Dean... Take. His. Assets."

Dean swallowed, then muttered a very hoarse, "Yes sir," before going off to do so. He didn't stop to see the look of hurt and disappointment on Bobby's face, though he knew it was there.

Bobby just watched, and when his shop was no longer a shop, the Winchesters loaded up their coach with everything.

Dean walked by Bobby, and wanted to say something to him, but couldn't think of anything. He wanted to tell him he wished things were different... that he had come to work with him... he wanted to thank him... wanted to apologize... but nothing came out.

Bobby leaned in instead.

"It's okay, son. No hard feelings between businessmen, right?" he said, and patted Dean on the shoulder, turning away from him.

Dean stood there, staring, until Sam tugged him to leave.

"That," Tessa sighed, "Was the last you ever saw of Bobby Singer."

"You're right," Dean said, then sniffling, asked, "C-can you tell me what came of him, Tessa?"

"Oh, Bobby? He became an old drunk, a poor one at that."

Dean grimaced, and Tessa went on. "But... he may have lost his business, and his money... though he never lost any of his friends."

Dean nodded sadly. "I don't doubt it, the man had a heart of gold."

"Yet you closed his business on Christmas."

Dean found himself grimacing again, and shook his head. Suddenly, he became angry again. "Take me home, why won't you?! I can't do anything to fix what I did all these years ago."

Tessa just waved her hand, and this time, it was about five years after the last Christmas. They were in Sam's home, and he was talking to a woman.

"Jess," Dean noted, smiling a little. Then his face saddened, thinking about what had come of that, while evidently witnessing it as well.

"I haven't _changed_ , Jess!" Sam insisted, dismissing his fiancé, and the pretty blonde girl looked at him indignantly.

"Maybe you don't see it... but I remember when you talked about your dreams, your ambitions to open your own law firm! What happened to that?! Sam, you've changed- and not respectably."

"I won't have you telling me how respectable I am," Sam snapped, "God, you keep going on these rants lately! I'm one of the richest men in town, can't you just appreciate that, shut up and be happy?"

" _No_ ," Jess said, almost pleadingly, "Because you aren't. You're the furthest from happy I've ever seen."

Sam stared at her. "Then you don't know me very well, do you?"

Dean cringed, and shook his head.

"Ouch, Sammy!" He commentated, and Sam went on.

"You're making this bigger than it should be," he said in exasperation, "I've got work to do, okay?"

Jess narrowed her eyes, and stood up. "I can't believe it. The Sam I knew and fell in love with is gone! Don't you remember when we first met?! You asked me what you would do without me... I said you would crash and burn?"

Sam scoffed. "We were young, and stupid. I can obviously hold my own without you."

Jess was speechless, and Dean could see the hurt etched in her face. Finally, she spoke.

"I'll be going."

"Good. I _won't_ be seeing you," Sam growled at her, and she sniffed as she left abruptly out the front door. "May you be happy in the life you've chosen," she whispered back, and began to cry as she left.

Dean blinked. His brother had said Jess had left when her father had moved professions, not... _this_.

The next scene was four years later, the Winchesters' office again, just as dark and cold as Dean presently kept it. Castiel was sitting at his desk, looking a little younger here with his hair slightly tousled and less tired lines under his eyes.

Suddenly, the door opened, and the undertaker, a large man with dark hair and creepy eyes, walked in.

Castiel looked up, and greeted him at the door.

"Hello... is there something I can help you with?"

"I'm Crowley, with Fergus & Rowena Funeral Home... I was called by the doctor," the man said, and Castiel's eyebrows knit.

"Oh, dear... I'll inform the elder Mr. Winchester right away."

He got up, and walked over to Dean's desk. Dean himself looked a little older than when they had last seen him, with more lines around his eyes as well. He had put on some muscle around his arms, but that was really the only improvement.

"Sir... your brother is dying."

"I know," Dean replied, without looking up.

Cas stood there awkwardly, and tried again.

"Um... Sam's... taking his last few breaths, sir."

Dean sighed, and looked up irritably. "If he's dying, he's dying, there's nothing I can do about it. I'll go see him when the work day's done, which is in a half an hour."

Cas sucked in a breath, and nodded. He wanted to go visit Sam himself just to see him off, but figured since the younger brother hadn't had a chance to get to know Castiel very well, he might not recognize him in his state of illness. He was very sad to hear Sam's sickness had gotten worse... it would indeed be strange without the younger Winchester at the office.

The undertaker raised his eyebrows. "I'm... sure I can get him to hold out that long."

Cas nodded, and watched as the man went upstairs.

A small part of him hoped with all his heart Dean didn't catch anything fatal like his two siblings had. 

When seven o clock came around, Dean looked up. The real reason he hadn't gone to visit his brother alongside the undertaker was the sheer fright he had trapped within him of seeing his brother on his deathbed. It was still something Dean was denying; that Sammy wouldn't recover from his tuberculosis. His little brother, whom he had sworn to protect ever since dad died, was going to be gone soon. Sooner than soon- in the next hour or so, at most.

And that was something Dean just couldn't face;  it terrified the shit out of him. 

But he got up, and, closing his book, prepared himself for what was to come. He walked up the stairs, and made it to the bedroom, seeing Sam there in the same bed Jo had been those years ago. At least Sam was a little more coherent than she was at the time.

"Dean?" Sam mumbled, squinting. Dean went over to join his brother at his bedside.

"Yeah, it's me Sam..." he said hesitantly, "How're you doin'?"

"How do you think?" Sam coughed bitterly, and Dean looked down, sitting down beside him, rubbing a hand over his face.

"Sammy, I can't lose you too. I lost Jo, and dad, and... god, what am I gonna do all by myself?"

Sam coughed again, a wet, gurgley sound. "You're not by yourself. You've got Cas."

Dean frowned, drawing back. "What?"

"You're such an idiot," Sam wheezed, drawing a burdened breath, then he pulled Dean close by his collar.

"It's too late for me. I was wrong... but you... _you,_ can start over. Don't grow old the way dad did... Open your eyes. It's obvious Castiel-"

Suddenly, he fell into a fit of coughing. He clutched his chest, and Dean sat up worriedly as his brother fell limp against the pillow. "Sam? Sammy?! Hey! We need a doctor!!"

Evidently, they did not need the doctor, but the undertaker. Crowley came in, placing the sheet over Sam's head, and Dean felt everything holding his heart together dissolve in seconds. He cursed Christmas... it had brought him nothing but loss and sadness- why should he keep it so close to him?

"After this Christmas, you became a miser, even more so like your father. People feared and hated you," Tessa said, "Matter of fact, they still do."

"Gee," Dean muttered, "Thanks." 

Tessa shrugged. "Nothing but the truth. All except one man, who still has faith in you."

Dean looked over at her. "Do you mean...?"

Just then, loud chiming could be heard from all directions around the two, and Tessa suddenly winced.

"Looks like my time is up, Winchester."

"Oh, thank the good lord," Dean sighed.

Tessa smirked at him. "You'll thank _me_... one day."

Suddenly, everything went white, and Dean was back in his bed, curled in on his covers.


	3. Present

Two O' Clock.

Dean was frozen in his current position, unable to think of what to make of what just transpired, but his pondering was interrupted by the sound of happy snickering coming from the room across from him.

Dean, against all better judgement, cautiously got out of bed, and saw a bright, brilliant gold light shining from beneath the door. He could also smell something sweet in the air, emanating from the warm room, but couldn't make out just what. As he was about to cower off back to bed, he heard a voice.

"Get in here, Dean-o, and get to know me better!" More laughing followed this jovial invitation. 

Dean was thoroughly disturbed that there was, in fact, a _second_ spirit as foretold, and that it, as well as the last, was also on a first name basis with him. He slowly opened the door, and shielded his eyes from the light. It dimmed, and Dean looked up to see the second of the spirits stuffing his face with jellybeans and cookies. The fireplace in the room was crackling with a large fire, and the room was piled high with candies and delicacies galore.

"Hello, sugarloaf!" the little man grinned, and Dean was in awe of (and slightly frightened of) the tiny golden wings on his back. They were just as shiny and blinding as the light before him, and Dean squinted.

"Could you... tone it down a bit?" he asked, grimacing, and the man frowned, stepping closer.

"Oh, you think there are bright? Come see me in my true form someday, I'd like to see you keep your eyes after that. It's a common problem among us spirits of the present, y'know."

"There's more than one of you?" Dean asked, still scowling and shielding his eyes.

"Hells yeah! I got a ton of siblings- some aren't as nice as I am, though,so you're lucky I got the graveyard shift. I'm Gabriel, by the way. Pleased to make your acquaintance."

"Sure, pal..." Dean muttered, then sighed. "Can I just go back to bed? I've had a very long, unbelievable night, and a good few hours' rest would do me good."

"Sure," Gabriel shrugged, sucking on a candy cane now, "If you want to end up like your brother, I invite you to return to your bed."

This made Dean pause, and he turned back around wearily.

"Well," he said to himself, "at least the present'll probably be a little happier than the past."

"That's the _spirit_!" Gabriel grinned with an impish wink, and snapped his fingers, transporting them to a narrow cobble street in a blink.

Dean looked around sourly. "Why are we here? Looks like a dreary part of town."

"It's Christmas here too, y'know," Gabriel scolded, then pointed at the house in front of them.

"That's Castiel's house."

Dean seemed a little taken aback, and thought back to what Sam had been saying about the man in his escapade into the past. He turned his attention back to the present, and peered inside the window curiously. 

Gabe walked through the wall, and Dean stared. "You can do that?"

"So can you," Gabriel said, rolling his eyes, and pulled Dean through the door, hushing him as Castiel's family settled in before them.

"It's so nice of you to have us for Christmas," a man, who looked a lot like Castiel, said, smiling.

"Oh, of course, Jimmy!" Cas was saying, cooking something over the stove, "It makes my year seeing you three this time of the season."

"You need any help with the goose over there?" a woman asked, and Cas shook his head with a smile.

"I've got everything under control, Amelia, but thank you." Dean was startled to find that his heart was sinking... so, Cas had a wife. Good, good for him... 

Suddenly, a little girl, probably about seven years old, limped over with a crutch and gave Cas a big hug.

"I love you, Uncle Castiel," she murmured, and he picked her up, grinning. Dean blinked. _Uncle_... that wasn't his kid... that wasn't his wife. 

"No more than I love you, Claire-bear."

She giggled, and he put her down.

"Shall we go see what the pudding sounds like singing in the copper, sweetheart?" Amelia asked her, and she nodded excitedly, taking her mom's hand and limping with her to the next room.

Jimmy was left with Cas, and he sighed.

"She's not getting any better, Cas. Her condition is getting worse, I think." Dean did a double take. He had a twin brother?! Cas looked heartbroken at his twin's information, and this made Dean's chest ache.

"I wish I could do something."

"Oh, it's not your job to. But you do deserve better wages for what you work!"

Cas waved it off. "It's no big deal..."

"With that horrible boss of yours, too! Goodness, I don't know how you could be in love with him, Castiel, when all he does to return your feelings is work you overtime and underpay you!"

Dean's breath caught, and he watched in a suddenly paralyzed silence as Cas slumped into a chair beside Jimmy.

"I can't help it, Jimmy... he's just misunderstood, maybe. He's certainly been through a lot."

"He's always been so horrid to you!"

"Yes, but... he's lonely.... and attractive. I can't help it," Cas moaned, "I should hate him, I really should. But I can't hate someone who became this way because of hate. Show enough kindness, one day he may turn around and notice something more in me. Kiss me, take me to dinner, something."

Jimmy laughed. "That'll be the day. You know how society is about such business anyway, Castiel. It would have to be in the privacy of your own homes." Cas sighed dreamily, that far off look in his blue eyes that Dean sometimes catches at the office.

"I don't mind where it is... all that would matter would be the fact that he loves me back."

Dean turned, and stood slack-jawed beside Gabriel.

"Cas is... in love with me?" he whispered out, and Gabe smacked him upside the head.

"Bingo, muttonhead! Took you long enough. He's only been your faithful clerk for what, ten years, now? Pretty damn sad."

Dean stared down at his feet, thoughts swirling in his head. How could he have been _so_ stupid? Of course Cas was in love with him! Of course he was... this explained everything... but yet, it explained nothing at all. Why would Cas love someone like Dean? It just didn't make sense. Dean was sure he would die alone.

And he would. He didn't deserve Cas... Cas deserved someone better, someone good. Then another thought entered his head.

"Wait- Gabriel... will the girl be alright?"

Gabe turned to him. "Why're you asking me? Do I look like the spirit of the future to you?!"

"Well, no," Dean muttered, "But... I mean, c'mon, Gabe."

Gabriel sighed. "Look... that's not my realm, and I can't say for sure. But when I do take a peek, it looks like a crutch by the mantle, without an owner."

Dean clenched his jaw. "That can't happen. It can't!"

Gabe shrugged. "Hey, if she's gonna die, she'd better do it, right? Decrease the surplus population!"

Dean's eyes widened at his own words, and Gabriel smirked. The spirit snapped again, and the two were now in a house that wouldn't be considered as poor as Castiel's, but definitely not a mansion, at that. Dean looked around, and saw people sitting and laughing.

"Your cousin Charlie," Gabe explained, and Dean felt his heart pang.

"So he thinks Christmas is silly, and he believes it, too!" Charlie was saying to her guests, rolling her eyes.

"I don't see why you still visit him, love," her soft-spoken wife, who was wearing a beautiful pink dress, said, "Why don't you just let him be miserable by himself?"

There was a chorus of _'yeah'_ s, and Charlie frowned, shaking her head.

"I couldn't. I know he's grumpy, and snaps at me, and hates Christmas and all... but I feel sorry for him. He's all alone, and I'm his only living relative now. I feel I owe it to him to at least try once a year."

Gilda took her hand. "And that, my dear, is why I love you. You have room in your heart for everyone."

Charlie smiled, and kissed her. Then she turned back, and adjusted her green dress.

"Well... the only thing he did miss was a highly indigestible dinner, I suppose!" she joked, and Gilda swatted her.

"Oh, it was a lovely dinner!" a guest of theirs named Bess reassured, and Charlie shrugged.

"I don't know... I haven't much faith in these newlywed wives, have you, Mr. Fitzgerald?"

Another guest named Garth blinked once. "Oh, I couldn't speak on the subject. As a bachelor, I'm an outcast, and have no business doing so. Isn't that right, dear, lovely, unmovable Miss Bess?" he flirted, and Bess giggled.

Just then, someone began to play the piano, and Gilda encouraged everyone to dance while she pulled Charlie aside.

"I really don't think you should go and see him anymore. You're trying to squeeze happiness out of a stone, sweetie."

"I know," Charlie said, smiling sadly, "I just... sometimes I miss the days when I could come in, and he'd call me kiddo, and him and Sam would... show me how things worked in the business, and..."

Gilda kissed Charlie's cheek. "Hey. Dean's done this to himself. It's best you leave it with him now."

Charlie nodded, and turned.

"Well, to make fun of it all... let's play a game." The dancing stopped gradually, and everyone joined in excitedly.

"Let Charlie be "it", she's a natural at this!" Gilda said, sitting down and smiling.

Charlie grinned back. "Guess."

"Is it... a dessert?" one guest asked.

"No," Charlie said.

"A type of wood, perhaps?"

"No," Charlie offered, "More _alive_. Sort of."

"Does it have freckles?" Garth asked, and Charlie smiled.

"Used to."

"Is it a woman?"

"No."

"Are they in love?"

"Hell yes, but they probably don't know it."

Just then, Bess stood up, her drink sloshing.

"I know it! It's not food... it's not wood, either... it used to have freckles, and is not a woman, and is in love."

"What?!" Garth asked, and Bess laughed.

"It's Dean Winchester!"

"Yes," Charlie admitted, and they all had a good chuckle, which made Dean blush and feel just the least bit hurt.

"I don't wanna see anymore," he muttered to Gabriel, but Gabe just grabbed Dean's chin, swiveling his face so he was facing the vision. Seeing Charlie enjoying herself with her family started to put things in perspective for Dean... sure, Gilda was penniless, and didn't have a cent to her name, but they lived a life full of happiness... he'd never really been to their home and seen them together.

Dean tried to ignore the warm feeling he had from the vision, for he wasn't used to it and did not much wish to _become_ used to it.

Suddenly, Gabriel snapped again, and the vision of the dinner party and the last surviving Winchester besides Dean himself blinked into a different scene. This time, it was a graveyard, with thick fog rolling in at their feet.

Dean frowned. "Why're we here?"

Gabe sighed. "Welp honey toes, looks like my time with you is up."

"But... but you just started to show me Christmas!" Dean said, because he was starting to take a liking to this particular spirit, maybe even beginning to listen. Gabriel shrugged again.

"Tough luck, bucko. The present is short and fleeting- hey, like me! Any-old-who, one more teeny tiny thing before I go- there are two things you must beware."

Dean hesitated. "Alright... what are they?"

"Self deprication, and conformity."

"Huh?!"

"Beware them both, Dean Winchester, but most of all, beware the first. It will be your downfall... unless you change."

Dean heard these words echo in his ears as Gabe smirked, wiggled his eyebrows, and disappeared in a _poof_ of sweet-smelling golden sparkles.


	4. Future

Dean threw up his arms, and looked around... 

And that's when he saw it.

The cloaked figure, waiting at the other end of the graveyard. That must be...

Dean felt his throat tighten up. He feared this spirit more than any of them... seeing one's future could be a nerve-wracking thing, especially when told by your dead brother that it held nothing but torture and not-so-figurative chains. After a personal swearing match with himself, he hurried over, pulling his dressing gown tighter to his body, and stopped in front of the ghost.

"Are you... wh-who I think you are?" Dean asked nervously, but the specter did not move as he answered in a deep, ethereal drawl.

"That depends on who's asking."

Dean gulped at the spirit's intimidating voice and stature.

"D-Dean Winchester?"

"Ah... Dean," the ghost said, and removed the hood of his cloak, turning. He was bone-thin, with a sharp, eagle-like nose. He had a wisp of black hair, parted on the side and smoothed over. He was wearing a black overcoat underneath his long, billowing cloak.

"Are you the," Dean breathed, wetting his lips and swallowing, "The one who's supposed to show me my future?"

The spirit nodded, a sly smile creeping onto his face. "I am. My name is Death."

Dean huffed. "You're kiddin'... y'mean like, you're the grim reaper or something?"

The spirit considered this. "Or something," he replied calmly, and beckoned. "Keep up."

Dean knew better by now than to protest, and the spirit didn't lead them very far at all. They came to the undertaker, Crowley, who was older considerably older now, talking with someone at the graveyard, and approached.

"You should'a seen the bastard in life," the short Brit was saying to a gravedigger, and the two of them chuckled.

"Couldn'a been that bad, eh?" the gravedigger asked, and Crowley huffed.

"You'd be surprised. I was there when his brother died- who, for the record, was just as stingy as this one here- and it's no surprise the funeral was a meager one. Anyway, I've got some things to do... off to make a few pennies off of the cheap bugger."

The two said their goodbyes, and Dean frowned, nudging the spirit.

"I feel bad for the guy who they're talking about. Sounded like a real douchebag, though!"

Death just looked down at Dean's elbow from where it nudged him, and Dean cleared his throat, standing straighter.

"S-sorry... sir."

Death just stamped his metal cane once on the snowy ground, and they appeared just inside the warm doorway of-

"Cas' place!" Dean grinned, almost slapping Death on the back but refraining from doing so at the last minute, "Yeah, this place is always cheerful!"

But this time... it wasn't. He could hear crying, and Dean's smile faltered as he watched the handsome clerk sitting alone in the corner, by the fireplace and crying into his hands.

"Cas..." Dean whispered, going over to him, but he knew full well the other man couldn't see nor hear him. He wished he could just reach out and put a hand on Castiel's shoulder, because from how hard he was crying, it must be something pretty big. That, in itself, was a miracle for Dean to even think something as affectionate as that. It had been decades since he felt this way about anybody.

Suddenly, it began to dawn on Dean just what Cas might be crying about.

"No..." he muttered, whipping around to face Death, "No, it can't be..."

Death just stared at him gravely, and the door opened behind them. Cas attempted to make himself presentable as Jimmy and Amelia came in, hanging their coats and hats solemnly. Claire did not accompany them.

"Glad you could make it," Cas said quietly, feigning a smile, "How's she doing?"

"They... put her in the ground last Thursday," Jimmy said, his voice cracking as he, too, broke down. Amelia threw her arms around her husband, then when he had composed himself, went over to her brother-in-law.

"Dear... you must be just broken. First, our daughter, and now..." she sucked in a breath. "I know you loved him."

Cas just attempted to hold back any further tears. "N-no, it's... it's alright, I'm okay. Claire is truly happy now, I think... and, Dean-"

He stopped, unable to speak coherently, and lowered his head again into his clutch, shoulders shaking.

Dean, standing by the seat at the fireplace still, looked down, contemplating what he had just heard.

"What are they talking about?" he asked the spirit, dumbfounded, "Did I fire him or something? Or did he try to tell me he loved me, and I-I...? Why did they mention _me_?"

Death, once again, did not answer, only showed Dean the next vision. This one reintroduced the undertaker, Crowley, and a couple of other people he knew."There's Crowley again! And there's Miss Masters, my housekeeper... and my laundress, Anna! Why are they all gathered here?" Dean asked, and Death sighed.

"Shut up, Dean."

Dean closed his mouth, and turned to listen in again.

"Lookie at this," Meg drawled, "Doesn't do shit for us in life, and benefits us when he's dead!"

Anna giggled. "It's true... he paid me dirt for hours and hours of hard work."

"Well, he got what was coming to him," Crowley said, grinning devilishly, "Let's all put our junk out, shall we?"

"Ooh," Meg winked, "My, that's a little forward, even for me." 

Crowley rolled his eyes, and the owner of the trade shop came in. They began revealing things they had taken from the frequently-mentioned man in his death.

"I have: brooch, socks, comb, and pillow," Crowley said.

"I've got his blankets and pillow cases!" Anna smiled proudly, then Meg snorted.

"I've got his bed curtains- try and top that. And this pretty little gold necklace... never took it off, they would have wasted it if it weren't for me."

The owner frowned at her. "What do you mean, wasted it?"

"They'd have buried him in it!" Meg smirked, "but I took it off of him."

The owner grimaced. Everyone examined the bundles, and as the owner worked out the price and reward for each asset, Dean stepped forward, covering his mouth.

"That amulet Miss Masters took... that's mine! I never take it off! It belongs to me! All this, it's my stuff!"

Death looked over. "A bit slow on the uptake, Dean. But yes; all of it is yours." He put a hand on the man's shoulder. "One final vision."

Dean shielded his eyes, beginning to choke up. "No... no, please let me go back to bed! Please, let this all be a dream."

Death waited, then raised an eyebrow. "If you're quite finished, I can continue."

Dean swallowed, wiping his eyes shakily. "Yes sir."

When Dean opened his eyes, they were back in the graveyard.

"Why are we back in this God forsaken hell-hole?" Dean asked, and Death pointed at a headstone. It had snow over it, but Dean knew whose it belonged to.

"Wait..." he stuttered, "W-wait, I can change this. I can change!"

Death kept pointing to the stone.

"Come on," Dean said, his voice cracking, "Please!"

The spirit didn't answer, and Dean let tears fall as he fell to his knees, carefully and slowly brushing aside the snow.

**_DEAN WINCHESTER, January 1879-December 25th._ **

The year remained blocked with snow, but Dean knew. He squeezed his eyes shut, and shook his head.

"No... no! No, it can't be mine... Jesus, I'm only 34!"

"You might as well be an 80 year old oyster," Death deadpanned, "You sure act like one. After all, who would miss you? You saw what it would be like with you dead, just like your family. You're about to put on some weight, Dean," he grinned, and suddenly, Dean felt chains wrap around him and bind his arms.

"No! Why would you show me all of this if there's no hope at all? I can change this! Oh shit, spirit, I'll honor Christmas in my heart, I will, I'll be good! God dammit, I'll be good... I can change... I can change, Sammy was right... I CAN CHANGE!"

Dean's desperate sobbing continued as he fell into the black overcoat of Death.


	5. Christmas Day

Suddenly, he felt his arms wrapped around wood. The wood of a banister! And his arms were free, no chains!

Dean gawked, and got up, flying out of bed so fast he tripped and fell onto the floor. He got up quickly, grinning, and dusted off his knees. "I'm alive!" He shouted, and suddenly, Meg came in the door, carrying a platter.

"Good morning, sir," she grumbled to him, and Dean smiled.

"Hey, mornin', Meg! Merry Christmas!"

She stared at him funny. "Uh... sure. You too, I suppose."

Dean's grin grew even wider, and he bounced around his room. "Look! My bed curtains are still here! You didn't tear them down and sell them!"

Meg blinked. "Right..."

"Oh hell, I'm happy," he laughed, "I'm so stupid, and happy, and _ohhh_ , I have to go get to Cas, don't I?!"

Meg raised an eyebrow. "The attractive clerk?"

"Yes!" Dean cried, " _Exactly_ , the attractive clerk!"

Again, Meg looked at him funny with a hint of apprehension in her eyes, but Dean didn't care. He just grasped her hands, placing money into it. "Miss Masters... Merry Christmas, go have a good time," he smiled, and watched as Meg's face lit up (which was a rare occurrence). He was about to run right out the door with his robe on, if it hadn't been for Anna.

"Sir! Oh, sir, you're leaving dressed like that?"

Dean stopped, and regarded himself with a chuckle.

"Guess not," he decided, and ran back in, going to put a pressed suit on (not before dropping a heavy bag of coins in Anna's hands as well). He coiffed his hair perfectly, and took a deep breath; first he would play a little holiday trick on Cas, then finally confess what he had been waiting to for... well, ever.

He hummed to himself as he went out, waving to everyone. On the way to the poorer part of town, he saw Benny and Kevin again, out and about.

"Hey! Gentlemen!" Dean called, and ran after them, smiling again when they stopped. "Merry, merry Christmas to ya!"

Benny looked confused, and a little bit wary. "Uhm... thank you, sir," he nodded, and Dean placed a hand on his and Kevin's shoulders.

"I would like to apologize for my behavior yesterday. I don't know what the hell came over me. Anyway, will you put me down for-"

He whispered in Kevin's ear, and the man just about had a heart attack.

"Are you feeling alright, Mr. Winchester?!" He asked incredulously, and Dean clapped his hands together.

"Indefinitely better. Good day to you!"

Benny finally found his voice. "Th-thank you! That's so very generous of you!"

Dean smiled as he hopped off to Cas' house. He had to stop at a shop on the way there, and came out with a little something in his pocket. As he got nearer, he began to realize what he was about to do... he, _Dean_ _Winchester_ , son of stingy old John Winchester, was about to tell his underpaid, hopeful clerk that he loved him. It have him a warm fuzzy feeling thinking about that, because he did love him back, and Dean was about to become the happiest man in town, for certain.

He took another breath as he stopped in front of the door, and knocked sharply, putting on his hard, stony face. Amelia answered.

"Hello... what can I do for you?" She smiled wearily. Up close, she had a few more lines in her face from having to take care of Claire and such, Dean noticed.

"Yeah..." he said gruffly, "I'm Dean Winchester, is Castiel there?"

Her eyes widened, and Cas stopped what he was doing inside upon hearing his voice. "So this is what you look like... Yes, one moment please."

Dean nodded curtly, and she popped back inside. Just then, Jimmy came to the door, seemingly very angry.

"You've got a lot of nerve coming here!" He said, narrowing his eyes at Dean, "You already ruin his life, and now you've just gotta ruin his Christmas too, huh?"

Just then, Jimmy was yanked back, and Cas came running over, blinking his big blue eyes at Dean enough to make the green eyed money-lender quiver.

"I'm so, _so_ very sorry about my brother. He... hasn't taken his daily drugs."

"I don't take medicine!" They both heard, and Dean cleared his throat.

"Well... you weren't at work this morning."

Cas stuttered at this. "Um... forgive me, s-sir, but, I was there when you have me the day off."

Dean laughed coldly. "Me? Dean friggin' Winchester? Give YOU the day off? That's a good one, Novak." Cas bit his lip nervously, fidgeting and looking extremely disheartened. "Now... I won't take this kind of crap any longer. You leave me no choice..." he said, and Cas steeled himself to be fired or worse.

"...but to ask you to marry me."

Cas hesitated, freezing completely. Eventually, he shook his head. "I'm dreaming," he muttered to himself, "I just haven't woken up yet, that's all. Yes, that's all, that's all..."

Dean watched the man across from him mutter to himself about dreaming, and eventually just grabbed his face and kissed him. He didn't care who saw! Let it be known around town, around the _world_ , that they were in love!

"I..." Cas muttered, and Dean gave a small smile.

"I would love it if you became my dear husband, Castiel. If you'll have me, that is after all the shit I put you through. I don't deserve you."

"You don't," Amelia reiterated, but not without a smile. 

Cas blushed, and kissed Dean again. "Yes. A thousand times over, yes!"

There was clapping in the home, and Jimmy nodded. "About time."

Just then, little Claire came over, and Dean picked her up. "I'd also like to pay out Claire's medicine and help her get well again."

Cas (and the rest of his family) did a double take, and invited him in for a homemade brunch. Cas was still finding it hard to believe Dean's change of heart, and part of him wondered if his employer would simply return to his regular demeanor the next day. But as the morning went on, it was becoming evident just how strongly his own sentiments were truly returned by Dean.

A little bit later, Dean found himself marveling at the time past. He had gotten to know Jimmy and Amelia better, and felt as if Claire _was his own_ niece after playing with her for a while. He was tipsy off the atmosphere, the new, reinstated feeling of having a family again overwhelming him with tears.

He left later that evening with a promise to be back and help Cas move his things in with Dean in his (their) large house. Now, it was almost time to take Charlie up on her dinner invitation; he couldn't miss it for the world.

He walked back into town, whistling to himself, and made it to his cousin's house. Now, this visit he was even _more_ nervous about... he had no idea how Charlie would take this- how her wife would at that. Gilda seemed like a kind-hearted woman from what Gabriel had showed him, but of course, they had never officially met in person.

_It's funny, though, how much Charlie and even Gilda had reminded Dean of Jo. In so many ways, like Tessa had said._

He nodded once, biting his lip, and went up to the door, knocking. There was a pause, then a maid came to the door. She opened it, letting Dean in with a rather surprised look on her face, and took his hat and coat. Dean crept up to the door of the living room, and peeked in, knitting his eyebrows. He could hear the game being played, and as if they were scripted lines, he followed them.

"Is it... a dessert?"

"No."

"A type of wood, perhaps?"

"No. More _alive_. Sort of."

"Does it have freckles?"

"Used to."

"Is it a woman?"

"No."

"Are they in love?"

"Hell yes, but they probably don't know it."

" I know it! It's not food... it's not wood, either... it used to have freckles, not a woman, and is in love."

"Then what?!"

"It's- _oh!!_ "

Dean entered the room just as Bess was about to get the answer right, and everyone turned to look.

"Dean!" Charlie shouted incredulously, and got up. "God, it _is_ you! I never thought you'd..."

Dean blushed, rubbing the back of his neck. "I know... a grouchy son of a bitch like me's got a lot of nerve comin' here, huh? After the way I've treated you?"

Everyone remained quiet, and Charlie shook her head, coming over and wrapping him in a hug.

"No. No, you're _always_ welcome here."

Gilda, after a short pause, came over as well, placing her hand atop Dean's.

"You are," she smiled, and Dean couldn't help it. He hugged her too.

"We've never officially met," he said, "But I just want to say- Charlie couldn't have found a prettier, sweeter gal than you, Gilda. I'm lucky to know you, even if I'm a bit late to the game."

Gilda's smile became wider, and Garth hissed something to the piano player.

_"Hey- polka, play polka!"_

Music started, and with one last hug, Charlie encouraged her cousin to dance with her wife.

"Let's have a good time, you idjit," she laughed, and Dean grinned back, reveling in the feeling of it. He could be himself. He could be happy. John was dead, and so was Sam, but Sam hadn't left him. Sam had _helped_ him.

As they danced on Christmas night, Dean closed his eyes, finding himself thinking of the spirits of his own memory.

 _Thanks, brother,_ he thought, _you saved my ass. Wish I could talk to you again, this time under happier terms, but I can't say I want to join you just yet. Tessa, you little ball of fire... you helped me remember, so thanks for that. Gabe- I'll eat a cookie in your honor, 'cause you helped me see what I wouldn't open my eyes to. And Death- you talked some sense in to me, and now, I'm a changed man. Jo, my dear girl... I did it. I found true love._

 _It's a_ him _. And you'd love him. Oh, you'd love him._

"Merry Christmas," he said to his friends and family, "It's one hell of a good night."

-0-0-0-

**_Dean became a good man- he was true to his word, and better than it, for that matter. He and Cas got married, privately of course, but no less celebrated. Winchester and Sons became Winchester & Novak after Dean made his new husband a partner at the firm. Claire got well again, and her Uncle Dean spoiled her rotten, especially at Christmas, her (and his) favorite time of year. And as the highest paid clerk in the town observed in his gravelly, perfect voice, _ **

**_"Merry Christmas to all, and to all a good night."_ **

Chuck closed the book, took a long drink of whiskey, and disappeared ** _._**

THE END :)


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